70 Awkward Questions to Make a Guy Cringe

The primary purpose of having a conversation in dating is to get to know the other person. However, sometimes there is a need to pose some awkward questions simply because it is important for you to know the answers. You may also choose to ask an embarrassing question to your guy in order to observe how he reacts. How one carries themselves in an uncomfortable situation reveals a lot about who they are and how they think. First, we start with a list of unconventional questions ideal for a first or second date – for when you want to play it safe. These are good options when you feel it is too early to pull out the more uncomfortable and awkward ones. Read on for a list of queries which break the number one dating rule which advices against any discussion on past relationships. Then, we further defy the dating rulebook with some money-related questions. We have also prepared for you a list of direct questions to measure your guy’s commitment to the relationship to investigate exactly what he thinks of you. If you are wondering how far is too far, we have a few suggestions. We conclude with a list of questions which probably go beyond what your guy considers tolerable.

Awkward Questions to Ask Him

Unconventional Conversation Starters

These are fun out-of-the-box ideas of questions you could ask to get the conversation going. These are great for the first few dates when you are not very familiar with each other. They will not require him to reveal any embarrassing or particularly confidential information but the answers will definitely be interesting.
  1. Which part of the world would you never visit?
  2. If you had your way, how many hours would you sleep?
  3. If you could be reincarnated as an insect, which insect would you choose and why?
  4. Which grade/year of school did you enjoy the most?
  5. Which game character would you like to be and why?
  6. If you broke a world record for something, what would it be?
  7. What is the most indispensable app you have on your mobile phone?
  8. How many hours or days can you go without your mobile phone?
When you feel that you are significantly more comfortable with each other, you may attempt the more awkward questions. Some of these are more uncomfortable for you to ask while others are more challenging for him to answer.

1. The Thorny Ex Issue: Cringe-worthy Questions for Him

This is the one subject we are always advised to avoid in conversations with a new love interest: exes. Continuously babbling about past relationships generally communicates that you are not ready for a new one. This being a taboo topic, these questions will be outrageously embarrassing for him to answer.
  1. What, in your opinion, constitutes infidelity? Have you ever cheated on any of your past girlfriends?
  2. How often do you think about your ex? Does she cross your mind when you are with me?
  3. Do you keep in touch with your ex-girlfriends?
  4. How old were you when you first had sex?
  5. Have you ever had a one night stand while dating someone else?
  6. Which of your past relationships do you wish you had never gotten into?
  7. Why did your last relationship end?
  8. Have you ever used the ‘L’ word just to get something?
  9. How many people have you ever had sex with?
  10. Describe the most humiliating experience you have ever had?
  11. Have you ever accidentally sent a raunchy message to the wrong person?

2. Sticky Money Issues to Raise with a Guy

Money is a touchy subject. According to psychology experts, many people have a troubled relationship with money as individuals. When they are forced to share their money matters with someone else, things often take a turn for the worse. Here are a few sensitive money questions that will have him squirming in his seat.
  1. Are you in debt? Who do you owe and how much?
  2. How much can you afford to spend on an engagement ring?
  3. How many bank accounts do you have? How much money do you have in them?
  4. Would you describe yourself as a spendthrift or a penny-pincher?
  5. Can you afford to pay for this date?

3. Unnerving Questions of Commitment

It is not uncommon in a dating relationship to find partners with differing notions in terms of the seriousness of the relationship. You may believe that the relationship is headed in one direction while he believes something totally different. Here are a few awkward questions which will help put you both on the same page. They are embarrassing to ask because they presume a long-term relationship, which might not always the case.
  1. Do you see yourself settling down with me?
  2. How do you feel about children? How many would you want to have?
  3. What would you say if I insisted you get tested for STDs before we can get intimate?
  4. What would you do if another girl made passes at you in my presence?
  5. What would you do if I got pregnant?
  6. Do you believe in marriage? Would you like to get married one day?
  7. Would you like to have a family someday?
  8. How would you react if you discovered I was sleeping with someone else?
  9. If you had to choose between me and your mom, who would you choose?
  10. Do you enjoy spending time with your friends more than you do with me?
  11. How can I be sure that you really love me?

4. Uncomfortable Questions about You

What opinion does he have of you? This is a question many girls can’t quite answer. Here are a few questions to find out a little bit more about what he really thinks of you. By asking these questions, you are drawing attention to yourself. That is what makes it especially awkward to ask and even more uncomfortable to answer. You will certainly have him racking his brain to come up with appropriate answers.
  1. What do you find most attractive about me?
  2. Do you think this outfit makes my bum look big?
  3. Do you think your ex-girlfriend is prettier than me?
  4. How old do I look?
  5. Do you think I am overweight?
  6. Which of my girlfriends do you find sexiest?
  7. Do you think your family would like me?
  8. Are you in love with me?
  9. Do you think I am the kind of girl you could fall in love with?
  10. Was your ex-girlfriend a better kisser than me?
  11. Can you guess what I weigh?
  12. Does this dress make me look plump?
  13. What do you dislike most about my body?
  14. Can you guess how many men I have ever had sex with?

5. Other Awkward Questions to Ask a Guy

  1. Did you ever steal anything from a store? Did you get away with it?
  2. Have you ever been a drunk driver? If you have, have you ever got caught?
  3. What is the most embarrassing thing you have ever done in public?
  4. What do you think is the best way to kill someone and get away with it?
  5. Have you ever found yourself on the wrong side of the law?
  6. How much time do you need to prepare for a date?
  7. If I dared you to either kiss one of the guys in this room or walk down several busy streets in your birthday suit, which dare would you take?
  8. Have you ever watched hardcore porn?
  9. Would you let me sleep with your best friend if I thought he was hot?
  10. How do you feel about plastic surgery? Would you have any done on yourself?
  11. How many of the numbers in your phonebook are girls’ numbers?
  12. Have you ever experimented with drugs? Did you ever get addicted to anything?
  13. How would you feel about a makeover? Can I give you one?
  14. Do you consider yourself an emotional person? When was the last time you cried?
  15. Are you comfortable with your pot belly?

6. Questions You Would Rather Not Ask

Learning any skill consists of gaining an understanding of how to, as well as how not to achieve a goal. As you learn how to create a conversation while being on a date, here are a few questions you probably should steer clear from. These queries will probably offend your guy and may stretch the limits beyond what he is willing to tolerate.
  1. Did you ever peek and see your mother or sister naked?
  2. Have you ever suffered from an STD? What was your experience?
  3. Have you ever been responsible for someone’s death or serious injury?
  4. How can I be sure you are straight?
  5. Have you ever felt sexually attracted to a minor?

Bottom line

Different people react differently in embarrassing situations. As you have fun with these questions, be prepared for any answer or outcome. Some people may find these extremely offensive – in fact, offensive enough to cut short the date and leave. On the other hand, some people may enjoy the challenge presented and be happy to answer each one. If he does take you seriously and puts efforts into answering your questions, you are in for a fun and most engaging conversation.

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